I Asked 9 People About Lovers Significantly Older Than Them

I love love. I love all of its close and distant relatives too – lust, crush, infatuation. It’s all love to some degree.

I love the way love shimmies into our lives, all gussied up and ready to start a ruckus. I love how it smiles from the corner booth entirely unannounced. I love how it gets louder when we try to ignore it. I love that there’s so many different flavors – tart, sweet, rich, subtle. I love the adrenaline rush of lust-for-a-moment versus the warm, whisky in the belly heat of a love-that’s-here-to-stay.

Even when I am not in love, I still love it. I love watching it and hearing about it. Sometimes, on particularly solitary days, I think I prefer love from a distance. Tell me about yours, I could sit here all day. Couples holding hands in the street is my kryptonite.

Conversely, I love heartbreak almost as much as I love love. Some will call that ironic, but I would argue it is probably the most unironic thing about me. The gnawing ache, the one that infiltrates our bones like smoke, is a dark blue place that hurts so good. Where love is hazy, heartbreak is crystal clear. It is its own maddening form of romance.

Unexpected Romance is one of my favorite summer cocktails. I alternate between that and the fleeting He’s Just Here On Vacation From Paris, but they rarely have that at Happy Hour.

While there is a lengthy menu of Unexpected Romance varietals to choose from, they all have notes of connection. Feeling tingly for someone you never expected is, well, thrilling.

So this week, I asked readers if they’ve ever found themselves in an unexpected romantic tango with someone significantly older than them. Here’s what they said.

H – She was 42 and I was 23. She was the principal at my little sibling’s elementary school. We first met when I was dropping my sibling off one day. I know this sounds ridiculous, but we locked eyes across the room and I just knew something would happen. Finally, I ran into her at a bar in our town. We talked all night, she has a fantastic laugh. We’ve been dating for two years.

G – We knew each other through alumni networking and grabbed a drink together one night after a dinner for the group. 1 AM turned into 2 AM turned into 4 AM, you know the rest. I made the first move, but he had hit on me before. Age isn’t ~that~ weird, but he’s good friends with a guy who’s really senior at my company and we aren’t really at the public stage yet…so any time the guy gets brought up we dance around it. My friends think it’s hilarious. I’m 22, he’s 49.

C – Hooked up with my stepmom’s friend cuz I was drunk and she was drunk and I was driving her home after she got kicked out of the bar we were at. I was 20 she was in her 40s.

T – Me 26, her 47. So I actually approached her. I was nervous for sure, but I had just enough buzz going to not care enough. It was her daughters 21st birthday. While my buddies were focused on the early 20s girls, I had my sights on the older lady. We kept making eye contact here and there. I personally don’t think the age thing was weird at all. One thing that stood out was that she didn’t beat around the bush at all or anything. We both knew what we were looking for. The most memorable thing was her experience in the bedroom, not much was off the table. She was also very respectful and mature, I felt comfortable the entire time.

T– The most memorable thing for me is I felt hunted. Like most men, I think I’m cool and shit, and she made me feel like an inexperienced moron. Even in flirting, I could tell I was out of my league in several aspects and I love that. She was 47, I was 30.

P – He was 23 years older than me, we met in Italy while I took a year off from work to travel. He would read the paper in the morning at the coffee shop I would frequent. One morning I asked him his name, we got to talking and he bought me a coffee. He knew I was flirting, but he was cautious about my age. We connected over small things like playing cards and cooking together. I lived with him for three months before I returned to the states due to my mother’s health. We don’t communicate, but every once in a while, I get a postcard from him. It breaks my heart all over again.

S – She worked in a shop I went into and then happened to sit down next to me at the bar next door. Talked a little, then got her number. I didn’t think the age difference was much, but on the 2nd date when she grilled me about my age she laughed at herself with a look of “wow what have I gotten myself into”. I was halfway uncomfortable if she talked about her daughter (who I never met thank god). I would recommend for anyone who finds people their current age immature or lacking. Always a change of pace when you’re with older people. She was 34, I was 23.

N – He was 24, he was 34. He definitely cared a lot more about making me finish than hooking up with guys my age. He was a lot more open about wanting to talk about what we both liked in bed. We met at work…whoops.

J – I was at my grandparents’ house in Utah for Christmas. He worked at the lot where they sell Christmas trees. I thought he seemed really kind, like had sweet eyes. He gave me his number in case we had any problems. I laughed, because who has problems with Christmas trees? I texted him that week and he took me for drinks. He was such a good listener. We ended up hooking up a bunch, and he wanted to date. I knew it would never work, but every time I smell Christmas trees I think of him. He’s re-married now, and that makes me happy. He was 45 I was 25.

See what I mean! Couldn’t you just sit and listen to tales of fleeting love and lust and Christmas tree salesmen all day? Whether it’s for one night, or two years and counting – in the end, we never really know what’s coming, do we?

I dare say that’s the best part about love. It’s so gosh darn unexpected. .

Reading JR’s post yesterday was one of the most beautiful things i’ve read and I don’t even know him! Love is incredible, and the prospect of finding it, and the second hand happiness for those you care about that have found it, keeps me going every day. Great take!